RU2746139C1 - Growth stimulating agent for pre-sowing seed treatment - Google Patents
Growth stimulating agent for pre-sowing seed treatment Download PDFInfo
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- 239000002269 analeptic agent Substances 0.000 title claims abstract description 10
- 238000009331 sowing Methods 0.000 title claims abstract description 7
- 239000013543 active substance Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 239000004480 active ingredient Substances 0.000 abstract description 2
- -1 nitrogen-containing heterocyclic compounds Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- BFGQTWYXWNCTSX-UHFFFAOYSA-N triazine-4,5-dione Chemical class O=C1C=NN=NC1=O BFGQTWYXWNCTSX-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 150000004716 alpha keto acids Chemical class 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PFPYHYZFFJJQFD-UHFFFAOYSA-N oxalic anhydride Chemical compound O=C1OC1=O PFPYHYZFFJJQFD-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000020238 sunflower seed Nutrition 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 239000012224 working solution Substances 0.000 description 2
- 150000003920 1,2,4-triazines Chemical class 0.000 description 1
- HFBHPHBIBAUDNE-UHFFFAOYSA-N 2h-1,2,4-triazin-3-one Chemical class O=C1N=CC=NN1 HFBHPHBIBAUDNE-UHFFFAOYSA-N 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Изобретение относится к созданию новых регуляторов роста и развития растений из ряда азотсодержащих гетероциклов, а именно к соединениям производных 1,2,4-триазинонов, которые могут быть использованы в сельском хозяйстве.The invention relates to the creation of new regulators of plant growth and development from a number of nitrogen-containing heterocycles, namely, compounds of derivatives of 1,2,4-triazinones, which can be used in agriculture.
Известно применение азометинов 1,2,4-триазинов в качестве ростстимулирующего средства (патент РФ №2146251, кл. С07Д 253/06, А01N 43/707; 10.03.2000. Бюл. №7; патент США №4337082).Known use of azomethines 1,2,4-triazines as a growth-stimulating agent (RF patent No. 2146251, CL S07D 253/06, A01N 43/707; 03/10/2000. Bull. No. 7; US patent No. 4337082).
Недостатком является невысокая ростстимулирующая активность соединений и ограниченная область применения.The disadvantage is the low growth-stimulating activity of the compounds and the limited scope of application.
Близким по структуре (прототипом) является гексагидро-1,2,4-триазинон-3 (патент РФ №2379891, кл. A01N 43/707, А01Р 21/00; 27.01.2010. Бюл.№3).Close in structure (prototype) is hexahydro-1,2,4-triazinone-3 (RF patent No. 2379891, class A01N 43/707, A01R 21/00; 01/27/2010. Bull. No. 3).
Недостатком является недостаточная ростстимулирующая активность соединений и узкая сфера применения.The disadvantage is the insufficient growth-stimulating activity of the compounds and the narrow scope of application.
Изобретение решает задачу повышения продуктивности сельскохозяйственных культур.The invention solves the problem of increasing the productivity of agricultural crops.
Сущность изобретения заключается в создании биологически активного ростостимулирующего средства, содержащего в качестве действующего ингредиента производное гетероциклического ряда - 3-меркапто-1,2,4-триазинон-5, полученный на основе альфа-кетокислот и тиосемикарбазида.The essence of the invention lies in the creation of a biologically active growth-stimulating agent containing as an active ingredient a derivative of the heterocyclic series - 3-mercapto-1,2,4-triazinone-5, obtained on the basis of alpha-keto acids and thiosemicarbazide.
где R - СH3 (1), С6Н5 (2).where R is CH 3 (1), C 6 H 5 (2).
Получение новых соединений иллюстрируется следующими примерами.The preparation of new compounds is illustrated by the following examples.
Пример 1. Получение альфа-кетокислот.Example 1. Obtaining alpha-keto acids.
Метилпировиноградную кислоту получают в две стадии. На первой стадии в четырехгорлую колбу, снабженную механической мешалкой, обратным холодильником, капельно загружают 62,5 мл толуола, 5,75 г (0,25 моль) металлического натрия, и после расплавления последний при помощи мешалки диспергируют в гранулы диаметром не более 1 мм. Затем прикапывают 25 мл абсолютного спирта таким образом, чтобы реакционная смесь находилась постоянно в кипящем слое. После полного растворения металлического натрия реакционную смесь охлаждают до 25…30°С и прикапывают 21,75 г (0,15 моль) диэтилоксилата и 12,75 г (0,125 моль) этилового эфира карбоновой кислоты. Реакционную смесь выдерживают при температуре 40…45°С в течение двух часов, охлаждают до комнатной температуры и выливают в смесь 20 г концентрированной серной кислоты и колотого льда. Оксалиловый эфир извлекают экстракцией серного эфира. На второй стадии проводят гидролиз и декарбоксилирование оксалилового эфира. В трехгорлую колбу, снабженную механической мешалкой, обратным холодильником и термометром, загружают смесь из одного объема оксалилового эфира, четырех объемов воды и двух объемов концентрированной соляной кислоты, кипятят смесь в течение 6 часов. Затем реакционную смесь охлаждают и нейтрализуют раствором гидроксида калия до рН 6. Целевой продукт выделяют серным эфиром, сушат сульфатом натрия и отгоняют растворитель.Methylpyruvic acid is obtained in two stages. At the first stage, 62.5 ml of toluene, 5.75 g (0.25 mol) of metallic sodium are added dropwise to a four-necked flask equipped with a mechanical stirrer, reflux condenser, and after melting the latter is dispersed using a stirrer into granules with a diameter of not more than 1 mm ... Then add 25 ml of absolute alcohol so that the reaction mixture is constantly in a fluidized bed. After complete dissolution of sodium metal, the reaction mixture is cooled to 25 ... 30 ° C and 21.75 g (0.15 mol) of diethyloxylate and 12.75 g (0.125 mol) of ethyl ester of carboxylic acid are added dropwise. The reaction mixture is kept at a temperature of 40 ... 45 ° C for two hours, cooled to room temperature and poured into a mixture of 20 g of concentrated sulfuric acid and crushed ice. Oxalyl ether is recovered by extraction of sulfuric ether. In the second stage, hydrolysis and decarboxylation of oxalyl ether are carried out. In a three-necked flask equipped with a mechanical stirrer, reflux condenser and thermometer, load a mixture of one volume of oxalyl ether, four volumes of water and two volumes of concentrated hydrochloric acid, the mixture is boiled for 6 hours. Then the reaction mixture is cooled and neutralized with a potassium hydroxide solution to pH 6. The target product is isolated with ether, dried with sodium sulfate and the solvent is distilled off.
Физико-химические характеристики метилпировиноградной кислоты:Physicochemical characteristics of methylpyruvic acid:
Выход: 63%.Yield: 63%.
Т. кип. °С: 30-31.T. kip. ° C: 30-31.
К.ч., мл KОН/г: 483.C.ch., ml KOH / g: 483.
Масс-спектр, т/е: 116.Mass spectrum, m / e: 116.
Элементный анализ, %:Elemental analysis,%:
Элементный анализ, %:Elemental analysis,%:
Найдено (С): 47,03Found (C): 47.03
Вычислено (С): 47, 06.Calculated (C): 47, 06.
Фенилпировиноградную кислоту получают гидролизом 2-метилоксазолонов-5.Phenylpyruvic acid is obtained by hydrolysis of 2-methyloxazolones-5.
Физико-химические характеристики фенилпировиноградной кислоты:Physicochemical characteristics of phenylpyruvic acid:
Выход: 82%.Yield: 82%.
Т. пл. °С: 1541.T. pl. ° C: 1541.
К.ч., мл KОН/г: 341.C. ch., Ml KOH / g: 341.
Масс-спектр, т/е: 164.Mass spectrum, m / e: 164.
Элементный анализ, %:Elemental analysis,%:
Найдено (С): 65,73Found (C): 65.73
Вычислено (С): 65, 85.Calculated (C): 65, 85.
Пример 2. Получение производных 3-меркапто-1,2,4-триазинона-5.Example 2. Obtaining derivatives of 3-mercapto-1,2,4-triazinone-5.
В трехгорлую колбу, снабженную механической мешалкой, обратным холодильником и термометром, загружают 100 мл воды, 0,8 г (0,01 моль) гидрокарбоната натрия и небольшими порциями 0,1 моль альфа-кетокислоты, после полного растворения которой добавляют 9,1 г (0,1 моль) тиосемикарбазида. Реакционную массу кипятят 3 часа, охлаждают до 10°С и нейтрализуют концентрированной соляной кислотой до рН=6,0. Выпавший осадок отфильтровывают, промывают водой и сушат на воздухе. Для увеличения выхода целевого продукта фильтрат обрабатывают концентрированным раствором гидроксида натрия и выдерживают в условиях синтеза 1 час. Выпавший осадок отфильтровывают, промывают водой и сушат на воздухе.In a three-necked flask equipped with a mechanical stirrer, reflux condenser and thermometer, load 100 ml of water, 0.8 g (0.01 mol) of sodium bicarbonate and 0.1 mol of alpha-keto acid in small portions, after complete dissolution of which 9.1 g is added (0.1 mol) thiosemicarbazide. The reaction mass is boiled for 3 hours, cooled to 10 ° C and neutralized with concentrated hydrochloric acid to pH = 6.0. The formed precipitate was filtered off, washed with water, and dried in air. To increase the yield of the target product, the filtrate is treated with a concentrated sodium hydroxide solution and kept under the synthesis conditions for 1 hour. The formed precipitate was filtered off, washed with water, and dried in air.
6-Замещеные 1,2,4-триазиндионы-3,5 представляют собой твердые вещества, от белого до оранжевого цвета, растворимы во многих органических растворителях.6-Substituted 1,2,4-triazinediones-3,5 are white to orange solids, soluble in many organic solvents.
Физико-химические характеристики 6-метил-3-меркапто-1,2,4-триазинона-5 (1):Physicochemical characteristics of 6-methyl-3-mercapto-1,2,4-triazinone-5 (1):
Т.пл. °С: 258.M.p. ° C: 258.
ИК-спектр, см-1: 1690,3, 1550.IR spectrum, cm -1 : 1690.3, 1550.
УФ-спектр, нм: 221.UV spectrum, nm: 221.
Физико-химические характеристики 6-фенил-1,2,4-триазиндиона-3,5 (2):Physicochemical characteristics of 6-phenyl-1,2,4-triazinedione-3,5 (2):
Выход: 90%.Yield: 90%.
Т.пл. °С: 280 (с разл.).M.p. ° С: 280 (with decomp.).
ИК-спектр, см-1: 1690, 1600.IR spectrum, cm -1 : 1690, 1600.
УФ-спектр, нм: 264.UV spectrum, nm: 264.
Пример 3. Лабораторные биологические испытания заявленного ростстимулирующего средства.Example 3. Laboratory biological tests of the claimed growth-stimulating agent.
Семена пшеницы, огурцов, редиса, вики раскладывал в чашки Петри и заливали 4 мл рабочего раствора. Затем чашки Петри помещали в термостат на двое суток при температуре 27°С. Рабочая концентрация препаратов - 0,1, 1, 10 мг/л. Повторность каждого варианта - 4-х кратная. Эффективность соединений определяли через двое суток по длине (1) и массе (т) этиолированных проростов. Результаты опыта приведены в таблице 1.Seeds of wheat, cucumbers, radishes, vetch were laid out in Petri dishes and 4 ml of working solution were poured. Then the Petri dishes were placed in a thermostat for two days at a temperature of 27 ° C. The working concentration of drugs is 0.1, 1, 10 mg / l. The repetition of each variant is 4-fold. The effectiveness of the compounds was determined after two days by the length (1) and weight (t) of etiolated seedlings. The results of the experiment are shown in table 1.
Пример 4. Вегетационные испытания заявленного ростстимулирующего средстваExample 4. Vegetation tests of the claimed growth-stimulating agent
Семена кукурузы и подсолнечника в течение 20 час. замачивали в исследуемых соединениях (рабочая концентрация 1-10 мг/л). затем обработанные препаратами семена кукурузы, подсолнечника высевались в вегетационные сосуды диаметром 25 см. Повторность каждого варианта 4-х кратная. Через две недели после посева по массе надземной части растений определяли эффективность соединения в сравнении с прототипом и контролем. Результаты опыта приведены в таблице 2.Corn and sunflower seeds for 20 hours. were soaked in the test compounds (working concentration 1-10 mg / l). then the maize and sunflower seeds treated with the preparations were sown in pots with a diameter of 25 cm. Each variant was repeated 4 times. Two weeks after sowing, the efficacy of the compound in comparison with the prototype and control was determined by the weight of the aboveground part of the plants. The results of the experiment are shown in table 2.
Пример 5.Example 5.
Обработанные препаратами в концентрации 10 мг/л семена ячменя, пшеницы, ржи высевали в вегетационные сосуды диаметром 25 см. Через две недели после посева проводили учет эффективности соединений путем замеров длины (1) и массы (т) надземной части растений. Данные приведены в таблице 3. Повторность каждого варианта - 4-х кратная.Seeds of barley, wheat, and rye treated with preparations at a concentration of 10 mg / l were sown in pots with a diameter of 25 cm. Two weeks after sowing, the effectiveness of the compounds was taken into account by measuring the length (1) and weight (t) of the aboveground part of the plants. The data are given in Table 3. The repetition rate of each variant is 4-fold.
Пример 6.Example 6.
Семена пшеницы, ячменя, проса раскладывали в чашки Петри и замачивали 4 мл рабочего раствора. Затем чашки Петри помещали в термостат при температуре 27°С. Через три дня определяли энергию прорастания семян, а через семь дней - схожесть семян в сравнении с контролем и взятым прототипом. Результаты испытаний приведены в таблице 4.Seeds of wheat, barley, and millet were placed in Petri dishes and soaked in 4 ml of the working solution. Then the Petri dishes were placed in a thermostat at a temperature of 27 ° C. After three days, the germination energy of the seeds was determined, and after seven days, the similarity of the seeds in comparison with the control and the taken prototype. The test results are shown in Table 4.
Приведенные в таблицах 1, 2, 3, 4 данные показывают, что новые заявленные соединения в концентрации 1-10 мг/л проявляют ростстимулирующий эффект, что сказывается в увеличении длины (1) и массы (m) проростков и растений.The data given in tables 1, 2, 3, 4 show that the new claimed compounds at a concentration of 1-10 mg / l exhibit a growth-stimulating effect, which affects an increase in the length (1) and weight (m) of seedlings and plants.
Заявленные новые ростстимулирующие средства по степени эффективности превосходит взятый прототип.The declared new growth-stimulating agents are superior in efficiency to the prototype taken.
Таким образом, заявленные новые соединения обладают ростстимулирующей активностью и представляют практический интерес в качестве ростстимулирующего средства при предпосевной обработки семян.Thus, the claimed new compounds have growth-stimulating activity and are of practical interest as a growth-stimulating agent for pre-sowing seed treatment.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU765270A1 (en) * | 1978-06-14 | 1980-09-23 | Институт Органической Химии Им. Н.Д.Зелинского Ан Ссср | Octahydroimidazo-/4,5-e/-thiazolo-/3,2-b/-1,2,4-triazinediones-3,7 and their preparation method |
| EP0438717A2 (en) * | 1990-01-26 | 1991-07-31 | Bayer Ag | Trisubstituted 1,2,4-triazine-3,5-diones and intermediates |
| RU2208011C1 (en) * | 2002-01-08 | 2003-07-10 | Мазитова Алия Карамовна | Derivatives of 1,2,4-triazinediones exhibiting growth-regulating activity |
| EP2903981B1 (en) * | 2012-10-04 | 2016-05-11 | Bayer CropScience AG | 1,2,4-triazin-3,5-dion-6-carboxamide derivatives and their use as herbicides |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU765270A1 (en) * | 1978-06-14 | 1980-09-23 | Институт Органической Химии Им. Н.Д.Зелинского Ан Ссср | Octahydroimidazo-/4,5-e/-thiazolo-/3,2-b/-1,2,4-triazinediones-3,7 and their preparation method |
| EP0438717A2 (en) * | 1990-01-26 | 1991-07-31 | Bayer Ag | Trisubstituted 1,2,4-triazine-3,5-diones and intermediates |
| RU2208011C1 (en) * | 2002-01-08 | 2003-07-10 | Мазитова Алия Карамовна | Derivatives of 1,2,4-triazinediones exhibiting growth-regulating activity |
| EP2903981B1 (en) * | 2012-10-04 | 2016-05-11 | Bayer CropScience AG | 1,2,4-triazin-3,5-dion-6-carboxamide derivatives and their use as herbicides |
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| Antimalarials. 3. 1,2,4-Triazines. MARCH; BAJWA; LEE; WASTI; JOULLIE "Journal of medicinal chemistry", 1976, vol. 19, N6, p. 845 - 848. * |
| Antimalarials. 3. 1,2,4-Triazines. MARCH; BAJWA; LEE; WASTI; JOULLIE "Journal of medicinal chemistry", 1976, vol. 19, N6, p. 845 - 848. Derivatives of 1,2,4-Triazin-5-one. KHAMAEV, V. KH.; DANILOV, V. A.; KHANNANOV, R. N.; MAZITOVA, A. K., Russian Journal of Organic Chemistry, 1994, vol. 30, N5.2, p. 825 - 829. * |
| Derivatives of 1,2,4-Triazin-5-one. KHAMAEV, V. KH.; DANILOV, V. A.; KHANNANOV, R. N.; MAZITOVA, A. K., Russian Journal of Organic Chemistry, 1994, vol. 30, N5.2, p. 825 - 829. * |
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